Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

Guzman, Juan

doi:10.3390/molecules191219292

Cited by 330 publications

(269 citation statements)

References 162 publications

(235 reference statements)

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“…) inhibit the growth of multiple bacteria and fungi including S. aureus , S. pyogenes and C. albicans . Simple esters of cinnamic acid such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, octyl, phenyl and benzyl cinnamates showed MIC values against S. aureus and C. albicans in the ranges 50–301 μ M and 14–61 μ M, respectively . 3,4,5‐trihydroxycinnamic acid, a synthetic derivative, possessed EC 50 values of 0.63 μ M against S. epidermidis and 1.26 μ M against S. aureus .…”

Section: Antimicrobial Activitiesmentioning

confidence: 99%

Cinnamic acid derivatives in cosmetics: current use and future prospects

Gunia‐Krzyżak

Słoczyńska

Popiół

et al. 2018

Intern J of Cosmetic Sci

135

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Cinnamic acid derivatives are widely used in cosmetics and possess various functions. This group of compounds includes both naturally occurring and synthetic substances. On the basis of the Cosmetic Ingredient Database (CosIng) and available literature, this review summarizes their functions in cosmetics, including their physicochemical and biological properties as well as reported adverse effects. A perfuming function is typical of many derivatives of cinnamaldehyde, cinnamyl alcohol, dihydrocinnamyl alcohol and cinnamic acid itself; these substances are commonly used in cosmetics all over the world. Some of them show allergic and photoallergic potential, resulting in restrictions in maximum concentrations and/or a requirement to indicate the presence of some substances in the list of ingredients when their concentrations exceed certain fixed values in a cosmetic product. Another important function of cinnamic acid derivatives in cosmetics is UV protection. Ester derivatives such as ethylhexyl methoxycinnamate (octinoxate), isoamyl p-methoxycinnamte (amiloxiate), octocrylene and cinoxate are used in cosmetics all over the world as UV filters. However, their maximum concentrations in cosmetic products are restricted due to their adverse effects, which include contact and a photocontact allergies, phototoxic contact dermatitis, contact dermatitis, estrogenic modulation and generation of reactive oxygen species. Other rarely utilized functions of cinnamic acid derivatives are as an antioxidant, in skin conditioning, hair conditioning, as a tonic and in antimicrobial activities. Moreover, some currently investigated natural and synthetic derivatives of cinnamic acid have shown skin lightening and anti-ageing properties. Some of them may become new cosmetic ingredients in the future. In particular, 4-hydroxycinnamic acid, which is currently indexed as a skin-conditioning cosmetics ingredient, has been widely tested in vitro and in vivo as a new drug candidate for the treatment of hyperpigmentation.

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Section: Antimicrobial Activitiesmentioning

confidence: 99%

Cinnamic acid derivatives in cosmetics: current use and future prospects

Gunia‐Krzyżak

Słoczyńska

Popiół

et al. 2018

Intern J of Cosmetic Sci

135

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“…Cinnamic acid derivatives are produced by many different plants, and various natural products as well as synthetic analogs containing this feature have anticancer, 63 antifungal, 64 antimalarial, 65 and antimicrobial activities. 66 DBI-1, however, had no effect on viability of Vero cells (Supplemental Table 2) and did not have antimicrobial activity against wildtype S. aureus . Furthermore, limited SAR studies we have carried out show that the cinnamide moiety is not essential for activity against the tn::1050 strain, which is susceptible to D-alanylation inhibitors (Supplemental Table 3).…”

Section: Discussionmentioning

confidence: 97%

Accelerating the discovery of antibacterial compounds using pathway-directed whole cell screening

Matano

Morris

Wood

et al. 2016

Bioorganic & Medicinal Chemistry

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Since the introduction of penicillin into the clinic in 1942, antibiotics have saved the lives of millions of people around the world. While penicillin and other traditional broad spectrum antibiotics were effective as monotherapies, the inexorable spread of antibiotic resistance has made alternative therapeutic approaches necessary. Compound combinations are increasingly seen as attractive options. Such combinations may include: lethal compounds; synthetically lethal compounds; or administering a lethal compound with a nonlethal compound that targets a virulence factor or a resistance factor. Regardless of the therapeutic strategy, high throughput screening is a key approach to discover potential leads. Unfortunately, the discovery of biologically active compounds that inhibit a desired pathway can be a very slow process, and an inordinate amount of time is often spent following up on compounds that do not have the desired biological activity. Here we describe a pathway-directed high throughput screening paradigm that combines the advantages of target-based and whole cell screens while minimizing the disadvantages. By exploiting this paradigm, it is possible to rapidly identify biologically active compounds that inhibit a pathway of interest. We describe some previous successful applications of this paradigm and report the discovery of a new class of D-alanylation inhibitors that may be useful as components of compound combinations to treat methicillin-resistant Staphylococcus aureus (MRSA).

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“…Guzman [29] reported the antibacterial and antifungal activity of some phenolics when tested against bacterial and fungal reference strains. They reported antibacterial activity of rosmarinic acid against S. aureus, S. epidermidis, Pseudomonas spp., and E. coli.…”

Section: Discussionmentioning

confidence: 99%